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Our start-up is really getting some traction – yee ha! Now we need to bring a sales superhero on board, and I’m not sure how to separate the wheat from the chafe? I’ve made bad sales hires in the past where they show and tell me how amazing they are, and then they don’t close a single deal…sigh!

What should I be looking for? Is there a way to “test” them to see what real skills they’ve got? Any other tips hiring for this kind of role?

Many thanks,
From Start-up taking off!

Dear Start-up taking off,

I sat down with our VP of Sales, Eileen Wiens, and our Director of Sales Operations, Daniel Barber. Both have years of Sales interviewing experience; and have managed multiple teams. In fact, both interview candidates on a daily basis at ToutApp– they’re perfect for helping answer your question.

First and foremost, they both agree you should know how to sell to your uber driver. In other words, before you bring on a salesperson, make sure you can sell the product yourself. You’ll know what type of language you’re looking for in the interview, and will be able to define your product. So here’s your answer for how to hire an amazing salesperson…

Where do you start?

Know exactly what you’re hiring for. Eileen says, “Are you looking for hunters or farmers?” In other words, do you need someone qualifying or finding leads, or do you need “closers” or reps that can work on Enterprise accounts. It’s important to first understand each role and your sales cycle (transactional one-call close vs. complex 6-9 month cycle), and only then, will you know what your perfect candidate looks like. “You need to find the type of person that fits the type of sale that you have, it may evolve from SMB to Enterprise, but know what you need.”

Types of questions to ask.

You’ll want to be able to separate the great interviewers from the people that can actually execute. Eileen likes using layering questions, and pulling away the layers for each answer. An example might be:Q: Describe to me your sales process.A: After a lead, I do a demo.Q: How do you get demos? Are they inbound leads?A: No, I have to prospectQ: Tell me how you prospect? How do you pick who to call or email…

By asking open ended questions, you’ll get to see a candidate’s strategy, clock-speed, and thought process. How deep can they go? They should have learned a lot about their product and know how to explain it to you in layman’s terms.

With beginning roles, you’ll want to focus on personality characteristics like grit and persistence. For experienced reps (5+years), it’s really about knowing how complicated of a sales process they’re capable of managing. Eileen tells me, “If there are Stakeholders across 3+ departments before we even get a trial off the ground; it’s about knowing how to navigate and piece together org structures and understanding all of the groups with keeping the sale in mind.”

More Sample Questions, and what you’ll learn.

-Aptitude: Sell me your last companies product.-Passion: Lately, What are you doing to develop your sales profession…books, blogs?-Ownership: Tell me about an early time where you had to demonstrate responsibility.-Experience (for seasoned sellers): How did you manage your sales cycle?-Consistent Persistence: How many times do you think it’s worth following-up with someone? Hint: Most people drop after 5, be that sixth! :)-Critical Thinking: How is selling door-to-door similar to this role? Have them tell you how they would get someone to open the door for you (over the 200 other people ringing the doorbell). Hint: the inbox is the modern day doorstep.

Interview Style.

You’re going to be shocked to hear this. You’re doing it all wrong. Daniel, our Director of Sales Ops is going old-school…he doesn’t do phone screens! He asks me, “How much time does a phone screen take?” I answer 15-30 minutes. He asks, “How much time would that take in real life?” I answer 30 minutes. Because your allotted time is relatively the same (for first-round sales interviews), why wouldn’t you want to meet them in person? He goes on to say, “What you get from an in-person is attention to detail. It saves a whole round of interviewing.” Instead of having a phone screen, and then asking similar questions on the first round in-person, you get the same information in one. “It’s a win-win because you save time on your calendar, and they get a shot at presenting themselves in their best possible light.”

What else does this do? It creates a stronger networking bond. By meeting with someone in person, you can create mini advocates for your brand; even if you don’t end up hiring them. You’ll never know if you will in the future, or if they’ll be needing your product. An in-person handshake and 30 minute meeting goes a lot farther than a 30 minute blind phone call. And, If you’re still hesitant, follow Eileen and at least do video screens via skype.

Also, have them do a writing exercise. Daniel asks our candidates to write a sample email to a person at a very large company; a real person with a title they would be actually contacting. “It’s an example of their first day-to-day task that they’ll be doing.” Look for what kind of information they include like 10k reports, details, connections, etc.

Lastly, it’s the old adage: hire slow fire fast. You should spend far more time on the interview research process and have a pipeline of candidates. Daniel uses the 100 Rule from Greylock Partners (a VC firm that instructs hiring at Facebook and LinkedIn). The rule is: With 100 resumes or Linked profiles, from those you meet 15 in-person, and from those 15, you’ll find your candidate.”

*Shoutout to Andrew Riesenfeld, Daniel attributes a lot of his recruiting knowledge to him.

3 Musts.

For Daniel, there are three attributes in salespeople that are good indicators for success:

1. Attention to detail. If you’re a SDR sending a message to 50 salespeople, and you get a name wrong or have a grammatical error on the first line; there isn’t a conversation anymore. This is a big must-have.2. Work ethic. Sales teams are in the office very early; usually the first. Closing deals essentially means running your own business. If you don’t grasp that concept, how are you going to be successful? Your territory is your own business, so make sure they have this!3. Critical thinking. Have them walk you through contacting the VP of Sales at Adobe. Find out their play by play and their drive to succeed. How a salesperson thinks through selling is vital to the deals they’ll get.

Lastly, you have to just plain like ‘em.

Culture can mean more than their experience as a salesperson. Making sure a person meshes well and embodies your company’s values will directly impact the happiness of the team. In a lot of cases, sales skills can be taught, but values can not. Know what’s important to you in terms of culture.